[go: up one dir, main page]

CN102845422A - Antimicrobial compositions and methods - Google Patents

Antimicrobial compositions and methods Download PDF

Info

Publication number
CN102845422A
CN102845422A CN2012100341505A CN201210034150A CN102845422A CN 102845422 A CN102845422 A CN 102845422A CN 2012100341505 A CN2012100341505 A CN 2012100341505A CN 201210034150 A CN201210034150 A CN 201210034150A CN 102845422 A CN102845422 A CN 102845422A
Authority
CN
China
Prior art keywords
composition
polyalcohol
fatty acid
combination
antibiotic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN2012100341505A
Other languages
Chinese (zh)
Inventor
王丹黎
马修·T·斯科尔茨
苏米塔·B·米特拉
巴斯卡尔·V·韦拉马坎尼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Publication of CN102845422A publication Critical patent/CN102845422A/en
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/12Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02Acyclic compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N63/00Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/50Isolated enzymes; Isolated proteins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)

Abstract

The present invention is generally related to a product and process to reduce the microbial contamination on organic matter, such as processed meat, fruits and vegetables, plant parts, inanimate surfaces such as textiles and stainless steel, and in the mouth or on dental products. In particular, the invention is related to a product and process to disinfect surfaces using an antimicrobial composition containing an antimicrobial lipid, an enhancer selected from the group consisting of bacteriocins, antimicrobial enzymes, sugars, sugar alcohols, iron-binding proteins and derivatives thereof, siderophores, and combinations thereof, and optionally a surfactant.

Description

Bactericidal composition and method
The application be International Application PCT/US2004/029241 on April 10th, 2006 enter the China national stage, application number is 200480029760.X, denomination of invention is divided an application for " bactericidal composition and method ".
Technical field
The present invention relates generally to a kind of composition and method for reducing the germ contamination on organic substance (such as manufactured meat, fruits and vegetables, plant part) and other inanimate surfaces (such as fabric and stainless steel).This composition for example also can be used for being used for reducing the bacterial concentration in the mouth in the dental applications.
Background technology
Annual food origin disease all causes a large amount of diseases and death, some tissues estimate direct or indirect medical treatment cost each above 1,000,000,000 dollars.Common food pathogeny body comprises Salmonella, Listeria monocytogenes, Escherichia coli 0157:H7, Campylobacter jejuni, Bacillus cereus, and Norwalk viroids.The common meat products with polluting of the outbreak of food origin disease, fresh milk, or bird product is relevant, but fruits and vegetables also can be used as the source of food-borne disease.The surface, container, and other matrix can be as the source of polluting in the food.The recovery of food article, as twist thin beef, hot dog, Alfalfa Sprouts, and orange juice, showing needs food-grade and a cost-efficient broad-spectrum antiseptic solution.
For reducing among food and other surfaces and the composition of germ contamination on it generally include and use materials such as organic acid and chlorine-containing compound (such as clorox), the higher concentration of this material can affect the performance on processed surface.Use the composition of fatty-acid monoester to be used in recent years reduce bacterium on food such as bird (be disclosed in United States Patent (USP) 5,460,833 and 5,490,992 in) and the fruits and vegetables (being disclosed among the international open WO 200143549A).Fatty-acid monoester has been used in the dry compositions on the fabric, and this openly is in the applicant's that on May 17th, 2000 submitted to assignee's the common unsettled U.S. Patent application 09/572,549.They also are used on the contact lenses, and this is disclosed in United States Patent (USP) 4,485, in 029.Fatty-acid monoester in these compositions exists stability inferior to be restricted in other components.
United States Patent (USP) 5,804,549 disclose basically by the lanthionine that contains bacteriocin, are mixed with the composition that the nisin of glyceryl monolaurate forms, and the purposes that infects of the bacterium that belongs to for the treatment of Helicobacter of this composition.These preparations relate to by the mucous membrane system of impact protection microorganism and process intestines and stomach.
Summary of the invention
The invention provides have effective antibacterial activity composition for reducing on the organic substance (such as food), mammal skin, and mouthful in (that is, the oral cavity), and/or the microorganism level on the non-living material.Composition of the present invention comprises antibiotic lipid, and this antibiotic lipid is selected from the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative (ester or ether), and its combination.These compositions also comprise reinforcing agent.The reinforcing agent that is fit to can include, but not limited to bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore (siderophore), and its combination.Can use the various combinations of reinforcing agent when needing.
Other components that are included in the composition of the present invention are surfactant and other additives of various combinations.Composition can be conc forms, further mixes in water-based or non-aqueous excipient before using when perhaps needing.
In one aspect, the invention provides a kind of bactericidal composition, it comprises: antibiotic lipid composition, and it comprises and is selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination; And enhancer component, it comprises and is selected from following compound: iron-binding protein and its derivative, siderophore, and its combination.
In one aspect of the method, the invention provides a kind of bactericidal composition, it comprises: antibiotic lipid composition, and it comprises and is selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination; And enhancer component, it comprises organic acid and is selected from following compound: bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and its combination.
In one aspect, the invention provides a kind of bactericidal composition, it comprises: antibiotic lipid composition (preferably, the antibiotic lipid composition of main amount), it comprises and is selected from following compound: (C7-C14) polyunsaturated fatty acid ester of polyalcohol, (C8-C22) unsaturated fatty acid ester of polyalcohol, (C7-C14) saturated fatty ether of polyalcohol, (C8-C22) unsaturated fat ether of polyalcohol, its oxyalkylated derivative, with its combination, wherein oxyalkylated derivative has less than 5 moles of alkoxide/mole polyalcohol (preferably, antibiotic lipid composition does not comprise monoglyceride); Enhancer component, it comprises and is selected from following compound: bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and its combination; With the option list surface-active agent.
In one aspect of the method, the invention provides a kind of bactericidal composition, it comprises: antibiotic lipid composition, and it comprises and is selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination; Condition is that antibiotic lipid composition does not comprise monoglyceride; And enhancer component, it comprises and is selected from following compound: mannose, wood sugar, mannitol, xylitol, and its combination.
In one aspect of the method, the invention provides a kind of bactericidal composition, it comprises: antibiotic lipid composition, and it comprises and is selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination; Condition is that antibiotic lipid composition does not comprise monoglyceride; And enhancer component, it comprises and is selected from following compound: bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and its combination; Wherein the pH of composition is not higher than 6.
In one aspect of the method, the optional surfactant (that is, one or more surfactants) that also can contain of composition.The composition purposes that surfactant can be estimated is selected.The surfactant that is fit to comprises acyl-lactate, dioctyl thio succinate, lauryl sulfate, dodecyl benzene sulfonate, and (C8-C18) salt of fatty acid.
In another aspect of the present invention, the composition that contains the food-grade component preferably shows effective antibacterial activity, and can be to the taste of food and food article, quality, and color, smell, or outward appearance has adverse effect.This can be by assessing with blind flavor tests.For common prepared food thing (such as hamburger), should carry out blind flavor tests to the food that boils.If at the product of processing with contrast between the untreated product and do not have statistical discrepancy, think that so the food processed is to the taste of food and food article, quality, color, smell, or not impact of outward appearance.
In one aspect of the method, contain the composition of the component (such as multiple ester of the present invention and reinforcing agent) that usually is construed to food-grade (GRAS), preferably can not produce obvious toxicity and environmental problem.Many compositions of the present invention also are easy to process in processing factory, and compatible with process equipment.
In one aspect of the method, the present invention also comprises the method that makes food or other surface sterilizations.The method comprises makes food or surface contact with composition of the present invention.For some embodiment, composition concentrates, and the method is included in and is coated to before diluted composition of matrix.In certain embodiments, provide a kind of method, be included in and apply antibiotic lipid composition in one or more steps, and apply enhancer component.When using two or more step, for example, enhancer component can apply before or after antibiotic lipid composition.
In one embodiment, the invention provides and a kind of bactericidal composition is coated to method on the matrix.The method comprise will be mainly the antibiotic lipid composition of amount be coated on the matrix, antibiotic lipid composition comprises and is selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination; With enhancer component is coated on the matrix, enhancer component comprises and is selected from following compound: bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and its combination.Enhancer component can with antibiotic lipid composition simultaneously, before or after it, apply.
In another aspect of the present invention, preferably, use described preparation and method, on matrix (for example, food article), can obtain total aerobic bacterium and count up to rare 1 log unit and on average reduce (that is the various bacteria that, causes food spoilage).This can use has original intrinsic bacterial concentration and is 10000-100, the thin beef sample of strand of 000 bacterium/thin beef of gram strand, when applying the capacity composition, so that 1% antibiotic lipid is applied to when twisting on the thin beef, measure according to the described method of embodiment 5-7.More preferably, composition of the present invention realizes that at least 2 log units on average reduce, and more more preferably at least 3 log units on average reduce.Most preferably, composition of the present invention is eradicated intrinsic bacterium (so that can not detect bacteria levels) fully.
In particular formulations, composition can be by the organic substance inactivation.That is, composition of the present invention is at blood, serum, and fat, and in the presence of other organic substances that food is found, be active usually, and be known that these materials can make other antibacterial agents such as iodine and quaternary ammonium compound inactivation.
In one aspect of the method, the invention provides a kind of ready-made antibiotic preparation, it comprises the fatty acid propylene glycol ester of the main amount that contains at least 60% fatty-acid monoester, the reinforcing agent of minor amount, with the option list surface-active agent, wherein greater than 30wt-%, the concentration of reinforcing agent is 0.1wt-%~30wt-% in ready-made preparation to the concentration of fatty acid propylene glycol ester in ready-made preparation.
In one aspect of the method, the invention provides a kind of kit and comprise the first container and second container, the first container comprises antibiotic lipid composition, antibiotic lipid composition comprises and is selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination (preferably, the first container comprises main amount (C7-C14) fatty acid propylene glycol ester), second container comprises enhancer component, enhancer component comprises and is selected from following compound: bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and its combination.
In selectable embodiment, this kit comprises the first container and second container, and the first container comprises (C7-C14) fatty acid propylene glycol ester of main amount and the composition of reinforcing agent, and second container comprises the second reinforcing agent.One or two container in the kit is optional also can to contain surfactant.This kit also can comprise label or packing insert, is used for showing the preferred mixed antibiotic preparation that can effectively reduce germ contamination with preparation of inclusion of the first container and second container.This label or the packing insert also show, antibiotic preparation can be coated to food, food article, or inanimate surfaces before be diluted.
Definition
" main amount " refers to that a kind of concentration of component is higher than any other single component.
" reinforcing agent " refers to strengthen the component that antibiotic lipid is renderd a service, thereby when using respectively the composition that lacks antibiotic lipid and lacking the composition of enhancer component, they can not provide the antibacterial activity same with composition in its entirety.For example, when lacking antibiotic lipid, reinforcing agent can not provide any appreciable antibacterial activity.The microbe species that humidification can refer to the degree of killing, kill speed and/or kill, and can not observe for all microorganisms.In fact, the enhanced level of killing is observed in the Gram-negative bacteria of being everlasting, such as Escherichia coli.Reinforcing agent can be synergist, thereby when mixing with the remainder of composition, the activity of composition in its entirety is greater than the composition that lacks enhancer component and the active summation that lacks the composition of antibiotic lipid.
" microorganism (microorganism) " or " microorganism (microbe) " refers to bacterium, saccharomycete, mould, fungi, mycoplasma, and virus.
" shelf-life " refers to used time of food spoilage of processing.For example, if count of bacteria is equal to or greater than 10 for certain skin area (1 square centimeter) 7(colony forming unit/square centimeter) thinks that so beef is corrupt.
" excipient " refers to the excipient that the component of composition is used.In bactericidal composition, the component that excipient normally exists with main amount.
Antibiotic " activity " comprises the activity to microorganism, includes but not limited to Gram-negative bacteria and gram-positive bacteria, fungi, fungal spore, saccharomycete, mycoplasma organism, and the virus of lipid coating.
Term in specification and claims " comprises " and its variant does not have limited significance.
Herein, " a kind of (a) ", " a kind of (an) ", " being somebody's turn to do ", " at least a ", and " one or more " exchange is used.
Here, the number range of end points comprises all numerals (for example, 1~5 comprises 1,1.5,2,2.75,3,3.80,4,5 etc.) in this scope.
Top summary of the invention is not intended to illustrate every kind of embodiment disclosed by the invention or enforcement.Following specification more particularly understands embodiment.Guidance is made by embodiment in some places in this application, can various combinations use these embodiment.In each case, list content only as representative, and should not be interpreted as unique content.To more know other features and advantages of the present invention from following detailed description and claim.
Embodiment
The present invention includes bactericidal composition (some of them are conc forms), and use the method for these compositions.
In one embodiment, concentrated bactericidal composition comprises antibiotic lipid composition, and it comprises that one or more are selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative (ester or ether), and its combination.Composition also comprises enhancer component, and it comprises that one or more are selected from following compound: bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and its combination.
Composition of the present invention also can comprise other additives, comprises surfactant and spices and covers the flavor agent.What comprise main amount at room temperature is those compositions of the antibiotic lipid of liquid, and antibiotic lipid is as the excipient of other components of antimicrobial activity and bactericidal composition.
Preparation can be used for processing and is polluted by Institute of Micro-biology or may be by the various matrix of its pollution.For example, composition can be used to process steel, glass, and aluminium, wood, paper, polymeric material, Formica, and other upper surfaces, ceramic tile, pottery, rubber, paper, and fabric, such as cotton, nylon, polypropylene non-woven, and linen.Other application of composition such as food and medical application, openly are in the applicant's that submitted on September 9th, 2003 assignee's the co-pending patent application 10/659,584 and 10/659,571.Other purposes of composition comprise dental applications.
Antibiotic lipid composition comprises that one or more are selected from following compound: the fatty acid ester of polyalcohol, the aliphatic ether of polyalcohol, its oxyalkylated derivative, and its combination.In certain embodiments, antibiotic lipid composition comprises and is selected from following compound: (C7-C14) polyunsaturated fatty acid ester of polyalcohol (preferably, (C8-C14) polyunsaturated fatty acid ester of polyalcohol), (C8-C22) unsaturated fatty acid ester of polyalcohol (preferably, (C12-C22) unsaturated fatty acid ester of polyalcohol), (C7-C14) saturated fatty ether of polyalcohol (preferably, (C8-C14) saturated fatty ether of polyalcohol), (C8-C22) unsaturated fat ether of polyalcohol (preferably, (C12-C22) unsaturated fat ether of polyalcohol), its oxyalkylated derivative, with its combination, wherein oxyalkylated derivative has less than 5 moles of alkoxide/mole polyalcohol.
Some embodiment comprises (C7-C14) fatty acid ester (preferably, (C8-C14) fatty acid ester), the unsaturated fatty acid ester of polyalcohol, the saturated fatty ether of polyalcohol, the unsaturated fat ether of polyalcohol, its oxyalkylated derivative, and its combination, wherein oxyalkylated derivative has less than 5 moles of alkoxide/mole polyalcohol.Specific embodiment comprises known (C7-C14) fatty acid ester (preferably, (C8-C14) fatty acid ester), such as glyceryl monolaurate, Capmul MCM C10, Capmul MCM C8, and/or mono laurate propylene glycol ester, single capric acid propylene glycol ester, single sad propylene glycol ester.
Fatty acid ester is particularly suitable for the material standed for that deals with food and Surface Contact food, to reduce pathogeny body and the corrupt quantity in the food, because many monoesters are food-grade by report, usually be construed to food-grade (GRAS) material, product can be effective as food antiseptics and topical agent.For example, Kabara, J.of Food Protection, 44:633-647 (1981) and Kabara, J.of Food Safety, 4:13-25 (1982) report, LAURICIDIN (lauric monoglyceride, so-called glyceryl monolaurate), food-grade phenol and chelating agent also can be used in the food antiseptics system.Fatty-acid monoester has reached 50 years as the food-grade emulsifier in the food, such as pie and bread mass, and ice cream, margarine, and salad dressing.
Fatty-acid monoester, such as glyceryl monolaurate, Capmul MCM C10, Capmul MCM C8, single enanthic acid glyceride, and/or mono laurate propylene glycol ester, single capric acid propylene glycol ester, single sad propylene glycol ester, with single enanthic acid propylene glycol ester, for gram-positive bacteria, fungi, the virus of saccharomycete and lipid coating is active, but is not active usually for Gram-negative bacteria only.When fatty-acid monoester when reinforcing agent in the composition mixes, composition is active to Gram-negative bacteria.
Especially, preparation of the present invention can reduce the quantity of people's pathogeny body of food source in the meat.For example, they can be used for spraying and impregnation process meat, such as beef, and pork, bird, fish, and sheep is used.They also can be used for spraying and flooding further processing meat, as twist thin beef, twist thin pork, twist thin chicken, strand slow fire chicken, hot dog, sausage and pork luncheon meat.The pathogeny body of people's food source that the preparation that can be disclosed kills comprises, for example, and E.coli 0157:H7, Listeria monocytogenes, and Saliiionella serovars.
Preparation of the present invention not only can be used for removing people's pathogeny body from meat and meat products, and can make fruits and vegetables corrupt and their shelf-life had a negative impact because of people's pathogeny body and other pathogeny bodies for the protection of other foods (such as plant and plant part).
Component in the composition provides antibiotic (comprising as a whole, for example, antiviral, antibacterium, or antimycotic) activity, thereby great majority are basically caused a disease or unwanted bacteriums, fungi, the virus of saccharomycete and lipid coating has wide spectrum and kills ability or make it be reduced to acceptable level.Should be appreciated that, in composition of the present invention, when independent consideration, the concentration of each component or amount can not killed microorganism receivable level, perhaps can not kill the unwanted microorganism of wide spectrum, perhaps can not kill fast; Yet when using together, each component provides (preferred collaborative) antibacterial activity (with using under the same conditions independent same component and comparing) of enhancing.
Those skilled in the art use analysis as known in the art and bacteria screening method, are easy to determine when composition of the present invention can provide antibacterial activity.A kind of analysis of easily carrying out is included under the preference temperature, with the predetermined bacteria levels in medium, make the known of selection or hold facile survival microbial strains, such as Escherichia spp., Staphylococcus spp., Streptococcus spp., Pseudomonas spp., or Salmonella spp., the engaged test composition.After enough times of contact, collect the sample of the bacterium that contains contact, dilution, neutralization launches at medium such as agar.The bacteria samples of launching was hatched 48 hours, the survival bacterium colony of growing on the counting culture plate.In case after obtaining the colony number, be easy to measure the minimizing of the bacterial number that test composition causes.Bacterium reduces usually to reduce with logarithm and comes record, by original inoculum number with contact afterwards inoculum and count log unit 10Between difference calculate.
Preferably, in the time of on being used in matrix, composition of the present invention is proved total aerobic bacterium and counts up to rare 1-log unit and on average reduce.For distinguishing enhanced activity and synergistic activity, can carry out the test board analysis.
The preferred composition of the present invention is physically stable.Herein, " physically stable " composition is can be because of a large amount of precipitations, and crystallization is separated etc. and the composition of significant change, and their original storage condition is under 23 ℃ at least 3 months, preferably at least 6 months.Particularly preferred composition is physically stable, when if 10-milliliter (10-ml) sample composition places the conical scale plastic centrifuge tube (Corning) of 15-ml, and use Heraeus Sepatech GmbH, Osterode, the Labofuge B of West Germany system, model 2650 with 3,000 rev/mins (rpm) centrifugal 10 minutes (2275 * g) time, so in the pipe bottom or the top can not observe and be separated.
The preferred composition of the present invention has good chemical stability.Like this especially for antibiotic fatty acid ester, ester exchange often occurs in it.After 50 ℃ of lower aging 4 weeks, preferred composition keeps at least 85%, and more preferably at least 90%, more more preferably at least 92%, more preferably at least 95% antibiotic lipid composition (three sample means) again.In airtight container, after 50 ℃ of lower aging 4 weeks, most preferred composition keeps average at least 97% antibiotic lipid composition.
The percentage conservation rate should be understood as that the percentage by weight of the antibiotic lipid composition of maintenance, by amount remaining in the aged samples in the airtight container that more can not cause degraded and the identical actual measured value that makes and at room temperature leave standstill 1~5 day sample (preferably with a collection of) contrast, measure the percentage conservation rate.For manifold composition, comprise that the part of antibiotic fatty acid ester preferably shows aforementioned stable.
Antibiotic preparation
Antibiotic preparation of the present invention can comprise one or more fatty acid esters, aliphatic ether, or its oxyalkylated derivative, and one or more reinforcing agents, and choose any one kind of them or the kinds of surface activating agent.Composition can be used for reducing the microorganism level, comprises Gram-negative and gram-positive bacteria on meat and other foods and the inanimate surfaces, virus, fungi and fungal spore, plant and plant part.Herein, " reducing the microorganism level " comprises bacteria growing inhibiting, promotes bacterium dead, and from plant or plant part, removes microorganism on the surface of meat and other foods and on the inanimate surfaces.
When composition in water when being suitable for being coated to concentration on the food and mixing, preferred its pH of preparation of the present invention is not higher than 6, more preferably, its pH is 4.5-5.5.
Antibiotic lipid
Antibiotic lipid provides the composition component of at least part of antibacterial activity.That is, antibiotic lipid has at least some antibacterial activities at least a microorganism.Usually being construed to is the main active component of the present composition.Antibiotic lipid can comprise the fatty acid ester of one or more polyalcohols, the aliphatic ether of polyalcohol, or its oxyalkylated derivative (ester and ether one or both of), or its combination.More specifically, antibacterial components can comprise that one or more are selected from following compound: (C7-C14) polyunsaturated fatty acid ester of polyalcohol (preferably, (C8-C14) polyunsaturated fatty acid ester of polyalcohol), (C8-C22) unsaturated fatty acid ester of polyalcohol (preferably, (C12-C22) unsaturated fatty acid ester of polyalcohol), (C7-C14) saturated fatty ether of polyalcohol (preferably, (C8-C14) saturated fatty ether of polyalcohol), (C8-C22) unsaturated fat monoether of polyalcohol (preferably, (C12-C22) unsaturated fat monoether of polyalcohol), its oxyalkylated derivative, and combination.
The fatty acid ester of polyalcohol is preferably formula (R 1-C (O)-O) n-R 2, R wherein 1(C7-C14) saturated fatty acid (preferably, (C8-C14) saturated fatty acid), or (C8-C22) residue of unsaturated (preferably, (C12-C22) unsaturated, how unsaturatedly comprise) fatty acid, R 2The residue of polyalcohol (common glycerine, propane diols, and sucrose), and n=1 or 2.R 2Comprise at least one free hydroxyl group (preferably, glycerine, propane diols, or the residue of sucrose).The fatty acid ester of preferred polyalcohol is to be derived from C7, C8, C9, C10, C11, and the ester of C12 saturated fatty acid.In the embodiment of glycerine or propane diols at polyalcohol, n=1, and when for sucrose, n=1 or 2.
Exemplary fatty-acid monoester includes but not limited to lauric acid (lauric monoglyceride), sad (SUNSOFT 700P-2), and the monoglyceride of capric acid (Sunsoft 767), lauric acid, sad, and the propylene glycol monoester of capric acid, and lauric acid, sad, and the sucrose monoester of capric acid.The fatty acid diester of exemplary fatty acid includes but not limited to lauric acid, and is sad, and the sucrose diester of capric acid.Other fatty-acid monoesters comprise oleic acid (18:1), linoleic acid (18:2), linolenic acid (18:3), and glycerine and the propylene glycol monoester of arachidonic acid (20:4) unsaturated (how unsaturatedly comprising) fatty acid.Generally well-known is that for example, 18:1 refers to compound and has 18 carbon atoms and 1 carbon-to-carbon double bond.
In certain preferred aspects, especially for those embodiments in the food article, the fatty-acid monoester that is applicable in the present composition comprises lauric acid, sad, and the known monoesters of capric acid, as be known as those of GML or commodity LAURICIDIN (the so-called lauric monoglyceride of lauric monoglyceride or glyceryl monolaurate) by name, Capmul MCM C10, Capmul MCM C8, the mono laurate propylene glycol ester, single capric acid propylene glycol ester, single sad propylene glycol ester, and combination.
The aliphatic ether of polyalcohol is preferably formula (R 3-O) n-R 4, R wherein 3(C7-C12) saturated fat base (preferably, (C8-C12) saturated fat base), or (C8-C22) unsaturated (preferably, (C12-C22) unsaturated, how unsaturatedly comprise) fat-based, R 4Glycerine, sucrose, or the residue of propane diols, and n=1 or 2.For glycerine and propane diols, n=1, for sucrose, n=1 or 2.Preferred aliphatic ether is the monoether of (C7-C12) alkyl (more preferably, (C8-C12) alkyl).
Exemplary fatty monoether includes but not limited to lauryl glyceryl ether, decyl glyceryl ether, octyl group glyceryl ether, lauryl propylene glycol, decyl propylene glycol, and octyl group propylene glycol.Other fatty monoethers comprise glycerine and propane diols monoether oil base (18:1), inferior oil base (18:2), and flax oil base (18:3), and arachidonic base (20:4) is unsaturated and polyunsaturated fat alcohol.The fatty monoether that is applicable in the present composition comprises lauryl glyceryl ether, decyl glyceryl ether, octyl group glyceryl ether, lauryl propylene glycol, decyl propylene glycol, octyl group propylene glycol, and combination.
The oxyalkylated derivative of above-mentioned fatty acid ester and aliphatic ether (for example, ethoxylation and/or propenoxylated derivative on all the other alcohol groups) also has antibacterial activity, as long as total alkoxy ester is relatively low.Preferred alkoxylate level is disclosed in United States Patent (USP) 5,208, among 257 (Kabara).At ester and ether during by ethoxylation, total mole of oxirane is preferably less than 5, and is more preferably less than 3.
The fatty acid ester of polyalcohol or aliphatic ether can be alkoxylated by routine techniques, preferred ethoxylation and/or propoxylation.Alkoxylated compounds is preferably selected from oxirane, expoxy propane, and composition thereof, and similar oxirane compound.
Composition of the present invention comprises one or more fatty acid esters that are fit to level, aliphatic ether, and oxyalkylated fatty acid ester, or oxyalkylated aliphatic ether, thus obtain results needed.When diluting with excipient, press the total restatement of composition, bactericidal composition can comprise that total amount is 0.01wt-% at least, preferred 0.10wt-% at least, the more preferably this material of 1wt-% at least.
Comprise one or more fatty-acid monoesters, the fat monoether, or the preferred composition of the present invention of its oxyalkylated derivative also comprise a small amount of two-or three-fatty acid ester (namely, fatty acid two-or three-ester), two-or three-aliphatic ether is (namely, fat two-or three-ether), or its oxyalkylated derivative.For the monoesters of propane diols, monoether, or oxyalkylated derivative preferably are no more than two-functionalised materials of 40%.For the monoesters of glycerine, monoether, or oxyalkylated derivative preferably only have a small amount of two-or three-functionalised materials.Under the fatty-acid monoester and fatty monoether situation of glycerine, press the total restatement of antibiotic lipid composition in the composition, preferably has the 15wt-% of being no more than, more preferably no more than 10wt-%, again more preferably no more than 7wt-%, again more preferably no more than 6wt-%, again more preferably no more than the diester of 5wt-%, diether, three esters, three ethers, or its oxyalkylated derivative.Herein, unless refer else, " fat " refers to have straight or branched alkyl or the alkylene moiety of the individual carbon atom of 6~14 (odd number or even numbers).
When using fatty acid propylidene ester, these esters in the composition can be used as two purposes of antibacterial activity body and excipient, and need not add another kind of water-based or non-aqueous solvent as independent excipient.4 ℃ or more relative superiority or inferiority be that other antibiotic lipids of liquid also can be used as excipient and antibacterial activity body.These concentrated compositions can improve effect, and obtain simultaneously stable composition, reduce use cost.
In certain embodiments, antibiotic lipid composition comprises (C7-C14) fatty acid ester (preferably, (C8-C14) fatty acid ester).In certain embodiments, antibiotic lipid composition comprises the aliphatic ether of polyalcohol, its oxyalkylated derivative, or its combination.
In certain embodiments, antibiotic lipid composition does not comprise monoglyceride.
In certain embodiments, it comprises antibiotic lipid composition and be selected from following compound: (C7-C14) fatty acid ester (preferably, (C8-C14) fatty acid ester), the unsaturated fatty acid ester of polyalcohol, the saturated fatty ether of polyalcohol, the unsaturated fat ether of polyalcohol, its oxyalkylated derivative, with its combination, wherein oxyalkylated derivative has less than 5 moles of alkoxide/mole polyalcohol.
Reinforcing agent
Composition of the present invention comprises reinforcing agent (preferably synergist), in order to strengthen antibacterial activity.Reinforcing agent can be selected from bacteriocin, antibiotic enzyme, iron-binding protein and its derivative, siderophore, sugar, sugar alcohol, and its combination.The compound of discussing below preferred reinforcing agent is selected from.
The bacteriocin that is fit to can comprise by lactic acid system used in the food preparation bacteriogenic those, comprise Lactobacillus, Lactococcus, Leuconnostoc and Pediococcus bacteriocin also can be found in C.Nettles and S.Barefoot, Journal of Food Protection, Vol 56, No.4, in April, 1993, page or leaf 338-356.The example of this bacteriocin includes but not limited to nisin and Pediocin AcH.Other examples of bacteriocin can prepare by gram-positive bacteria (comprising Staphylococcins) and list in Bacterio log unit ical Reviews, in September, 1976, other bacteriocins among the page or leaf 722-756.By the bacteriocin of Gram-negative bacteria preparation, as by Enterocins A and B, colistin (polymyxin e), large intestine bacteriocin E1, and polymyxin B bacterium also can be used as reinforcing agent.
Suitable antibiotic enzyme by the bacterium preparation can comprise lysostaphin and lysozyme, and common change or the recombinant forms of these enzymes, can be different from the native protein in the primary amino acid sequence.The example of the recombinant forms of lysostaphin is disclosed among U.S. Patent Application Publication 2002/0006406 (lysostaphin analog) and the U.S. Patent Application Publication 2003/0215436A1 (lysostaphin polymer conjugate).
The iron binding compounds comprises little siderophore and iron-binding protein and its derivative.
The iron that is fit to comprises that in conjunction with siderophore molecular weight less than 1000 dalton (usually, 400-1000 dalton) organic molecule, this organic molecular species is discharged by bacterium under the iron limited form, so that the ferric iron coordination, and prevent ferric hydroxide precipitate in natural environment.They are comprised of azanol hydrochlorate and phenates derivative, thereby provide high affinity coordination to ferric iron.The example of this molecule is with the synthetic high affinity iron chelator of bacterium, includes but not limited to intestines chelating element (enterobactin), vibrocin, Anguibactin, green pus bacterium chela ferritin, pyofluorescein, mycobactin, the outer chelating element of iron, Aerobactin, and desferrioxamine.
The iron-binding protein that is fit to comprises lactoferrin and its derivative, particularly from its derivative peptide (for example, lactoferricin B, lactoferricin H is derived from the enzymolysis of lactoferrin and activin) and siderophillin.In certain embodiments, lactoferrin is preferred reinforcing agent.
The steamed bun stuffed with sugar that is fit to is drawn together monose and disaccharides.The monose that is fit to includes but not limited to mannose, wood sugar, maltose, sorbose, and their corresponding sugar alcohols, mannitol, xylitol, maltitol, and sorbitol.In certain preferred aspects, sugar is selected from mannose, wood sugar, mannitol, xylitol, and its combination.In certain embodiments, sugar is the disaccharides of wood sugar alcohol and glucose.For disaccharides, at least a sugar is listed a kind of suitable monose preferably.The second sugar unit can be selected from the food article any suitable sugar commonly used, as but be not limited to glucose, fructose, mannose, wood sugar, galactose, sorbose, and sorbitol.
Should be appreciated that, can use various reinforcing agent combinations when needing.In some embodiments, by using reinforcing agent to obtain obvious effect.
Some composition of the present invention comprises the reinforcing agent of at least two kinds of inhomogeneous compounds, the reinforcing agent of preferred at least three kinds of inhomogeneous compounds.For example, some embodiment comprises the chosen from Fe binding proteins, siderophore, and at least a other reinforcing agents in the reinforcing agent of its combination and at least a inhomogeneous compound.
Optional, some embodiment comprises the chosen from Fe binding proteins, siderophore, and the reinforcing agent of its combination reaches at least two kinds of other reinforcing agents at least two kinds of inhomogeneous compounds.This other reinforcing agents can be selected from bacteriocin, antibiotic enzyme, sugar, sugar alcohol, and its combination.In one embodiment, enhancer component comprises nisin and lactoferrin.In one embodiment, enhancer component comprises nisin, lactoferrin, and sugar and/or sugar alcohol.
Comprise nisin, particularly with the composition of various non-bactericide combinations shown for various Gram-positives and Gram-negative bacteria have higher activity (referring to, for example, United States Patent (USP) 5,135,910; 5,217,950, and 5,260,271).Recently, in the presence of chelating agent, nisin to the bactericidal activity of other Gram-negative bacterias (comprising Helicobacter pylori) be disclosed (referring to, for example, United States Patent (USP) 5,304,540 and 5,334,582).Can not realize optimal bactericidal action under glyceryl monolaurate and the nisin, individualism, strengthen each other the bactericidal activity that Helicobacter is belonged to bacterial strain.Yet, containing the preparation of the nisin of glyceryl monolaurate, can effectively be applied on meat and other food articles as bactericidal composition.In certain preferred aspects, do not comprise nisin.
Other class reinforcing agent compounds, such as organic acid, chelating agent, phenolic compound, or alcohol (being disclosed in the applicant's who submits on the same day the common pending application (the reel number 58707US005 of agency)) also can be added in the bactericidal composition.The organic acid that is fit to comprises for example lactic acid, tartaric acid, adipic acid, succinic acid, citric acid, ascorbic acid, glycolic acid, malic acid, mandelic acid, acetic acid, sorbic acid, benzoic acid, and salicylic acid.In certain embodiments, enhancer component comprises organic acid and is selected from bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore, and the compound of its combination.In one embodiment, enhancer component comprises organic acid, lactoferrin, and Saccharide and saccharide alcohols one or both of.
The chelating agent that is fit to can comprise for example acidic sodium pyrophosphate, acidic sodium hexametaphosphate (such as the SPORIX acidic sodium hexametaphosphate), ethylenediamine tetra-acetic acid (EDTA) and its salt.The alcohol that is fit to for example can be ethanol, isopropyl alcohol, or long-chain alcohol, octanol and decyl alcohol.Phenolic compound, such as butylated hydroxyanisol, BHT, and TBHQ for example can strengthen the activity of fatty-acid monoester, and be the same with benzoic acid derivative, such as methyl, ethyl, propyl group, and butylbenzoic acid ester class.Other reinforcing agents that are fit to comprise in the applicant's who is that on September 9th, 2003 submitted to assignee's the co-pending patent application 10/659,584.In certain preferred aspects, the organic acid reinforcing agent is benzoic acid, and the phenolic compound reinforcing agent is methyl benzoic acid ester class (4-HBA methyl ester).
Surfactant
Composition of the present invention can comprise surfactant, is used for emulsification composition and helps wetting surface and/or help to contact microorganism.Herein, term " surfactant " refers to a kind of amphiphatic molecule, is defined the polarity that has simultaneously covalent bonding and the molecule of apolar regions.This term comprises soap, washing agent, emulsifier, surface active ingredient etc.Surfactant can be cation, anion, nonionic, or amphoteric.Comprise various conventional surfactants; Yet the surfactant of some ethoxylation can reduce or eradicate the antibiotic effect of antibiotic lipid composition.The preparation mechanism of this phenomenon is not also known, and the surfactant of ethoxylation that neither be all can play negative interaction.For example, poloxamer (polyethylene/polypropylene oxides) surfactant can be compatible with antibiotic lipid composition, but in some preparations, can not be compatible such as the sorbitol fatty acid ester of the ethoxylation of being sold with trade name TWEEN by ICI.Should be noted that, these are generalized concepts, and activity can be relevant with preparation, namely based on selection and the amount of the surfactant of used antibiotic lipid and ethoxylation.According to described in the embodiment part make preparation and and test antibacterial activity, those skilled in the art can easily measure the compatible ability of surfactant.When needing, can use the combination of various surfactants.
Anion surfactant, cationic surfactant, non-ionic surface active agent and amphoteric surfactant can be used for making the suitable emulsion of antibiotic fatty acid ester.For example, antibiotic preparation can comprise anion surfactant, such as acyl-lactate, and dioctyl thio succinate, lauryl sulfate, dodecyl benzene sulfonate, and (C8-C18) salt of fatty acid.The salt that is fit to comprises sodium, potassium or ammonium salt.Acyl-lactate comprises, for example, and stearyl-2-calcium lactate or sodium, isostearoyl base-2-sodium lactate, lauroyl-2-sodium lactate, caprylyl sodium lactate, cocoyl sodium lactate, and mountain Yu base sodium lactate.Ionic surfactant pack is drawn together glyceride, such as 12 glyceryls, four oleates; Sorbitol ester, such as the mono laurate sorbitol ester, commercial with trade name SPAN 20 from Uniquema International, Chicago, IL obtains; And the block copolymer of polyalkylene oxide (for example, PEO and poly(propylene oxide)), obtain from BASF (Parsippany, NJ) with trade name PLURONIC and TETRONIC.Dioctyl sulfo-sodium succinate commercial with trade name GEMTEX SC40 surfactant (40% dioctyl sulfo-sodium succinate in the isopropyl alcohol) from Finetex Inc., Spencer, North Carolina obtains.The caprylyl sodium lactate is commercial to be obtained from RITA (Woodstock, IL) with trade name PATIONIC 122A.NaLS is commercial from Stepan Chemical Co., Northfield, and IL obtains.
Be applicable in assignee's the co-pending patent application 10/659,584 that other surfactants in the bactericidal composition of the present invention are listed in the applicant who is that on September 9th, 2003 submitted to.
Application about food
Preparation of the present invention is specially adapted to reduce the level of food source property people pathogeny body, comprise Escherichia coli 0157:H7, Salmonella serotype, comprise S.typhimurium, Listeria (for example, L.monocytogenes), Canipylobacter (for example, C.jejuni), Shigella species, and Bacillus cereus.
The fatty-acid monoester that is applicable in the antibiotic preparation is considered to food-grade usually, GRAS, and/or be the food additive that U.S.'s food and FAD (FDA) are permitted.Especially, one or more are derived from C7-C12 fatty acid (preferably, C8-C12 fatty acid) fatty-acid monoester, such as Capmul MCM C10, Capmul MCM C8, glyceryl monolaurate, and/or single capric acid propylene glycol ester, single sad propylene glycol ester, the mono laurate propylene glycol ester can be used in the preparation of the present invention.Can regulate fatty-acid monoester to be fit to objective microbe.For example, when needs reduced plant or the lip-deep fungus levels of plant part, lauric acid monoester can mix with capric acid monoesters and/or sad monoesters.
Monoglyceride used among the present invention is usually with unreacted glycerine, monoglyceride, and diglyceride, and the form of mixtures of triglyceride obtains.Therefore, the preferred use contained higher concentration, for example, and greater than the material of 60wt-% monoglyceride.In some compositions, required material contains concentration greater than the monoglyceride of 85wt-% or 90wt-%.Useful especially commercially available material embodiment comprises glyceryl monolaurate (GML), from Med-Chem Laboratories, East Lansing, MI obtains with trade name LAURICIDIN, Monooctamoin (GM-C8) and monocaprin (GM-C10), from Riken Vitamin Ltd., Tokyo, Japan obtains with trade name POEM M-100 and POEM M-200 respectively, and obtain with trade name " MONOMULS 90L-12 " from Henkel Corp.of Germany those.Single sad propylene glycol ester (PG-C8), single capric acid propylene glycol ester (PG-C10), and mono laurate propylene glycol ester (PG-C12) is from Uniquema International, and Chicago, IL obtains.
In food applications, reinforcing agent is food-grade, and GRAS is listed, and/or the food additive of FDA-allowance.Enhancing dosage among the present invention can reach 20.0wt-%, preferred 1.0wt-%~10.0wt-%.In other embodiments, as comprise those of excipient, reinforcing agent can account for 0.01wt-%~1.0wt-%, preferred 0.01wt-%~0.5wt-%.Certain applications need the reinforcing agent of low concentration, avoiding taste of food, and quality, color, smell or outward appearance have unwanted change or variation.Depend on used specific reinforcing agent, can directly be mixed with dissolving and stable concentrate excipient in ester, maybe can be packaged in respectively in the suitable solvent.
In most compositions, use food-grade and/or GRAS surfactant, its amount provides the concentrate composition of 1.0wt-%~30.0wt-%, preferred 4.0wt-%~12.0wt-%.In comprising other embodiments of excipient, composition can comprise that concentration is 0.001wt-%~1.0wt-%, is preferably the surfactant of 0.01wt-%~0.5wt-%.
The concentration of the said components that the establishment bacterial growth is required depends on objective microbe type and used preparation (for example, the antibiotic lipid of existence, reinforcing agent, and the type of surfactant).When independent consideration, the concentration of every kind of component or amount, all can not kill composition as a whole the time such wide spectrum cause a disease or unwanted microorganism, kill rapidly, or the quantity of this microorganism be reduced to acceptable level.Therefore, when using together, compare with the component of using separately under the same terms, each component of preparation is to meat, plant or plant part, the surface of other processing provide strengthen or Synergistic antimicrobial active.The acceptable level of antibacterial activity usually among food or other surfaces or on surpass the 1-log unit and reduce.
Use instruction well known in the art and analysis, those skilled in the art are easy to really measure the effective dose of every kind of component.Can directly prepare and use composition of the present invention, or before using, be prepared into non-aqueous or the aqueous solution, emulsion or suspension.Normally management board is acceptable for the suitable excipient of preparation solution or suspension, such as FDA and Environmental Protection Agency USA (EPA).Acceptable especially excipient comprises water, propane diols, polyethylene glycol, glycerine, ethanol, isopropyl alcohol, and its combination.Optional, one or more antibiotic lipids can be used as excipient.
In preferred embodiments, glycerine monofatty ester accounts for the 0.001wt-%~30wt-% of antibiotic preparation, and reinforcing agent accounts for the 0.001wt-%~30wt-% of antibiotic preparation, and one or more surfactants account for the 0.001wt-%~30wt-% of antibiotic preparation.For example, ready-made preparation can comprise the fatty-acid monoester of 0.01wt-%~5.0wt-%, the reinforcing agent of 0.5wt-%~30wt-%, and the surfactant of 0.5wt-%~5.0wt-%.Especially, ready-made preparation comprises the fatty-acid monoester of 0.2wt-%~2.0wt-%, the reinforcing agent of 0.1wt-%~25.0wt-%, and one or more surfactants of 0.1wt-%~1.5wt-%.
The additional component of antibiotic preparation comprises, for example, the food-grade coating agent, such as beeswax, paraffin, Brazil wax, wax rhimba wax and Tissuemat E; Other coating materials comprise resin, shellac, wood rosin, zein; With prevent the component of preparation because of UV inactivation or decomposition, colouring agent, smell reinforcing agent, viscosity-control additive, such as Huang Shi glue, gum Arabic, carrageenan, carbomer (Carbopols) (B.F.Goodrich, Cleveland, Ohio), guar gum, and cellulose gum; Defoamer, such as the silicones defoamer, for example, and dimethyl silicone polymer (Dow Corning, Midland, MI), sticky agent, or spices are such as natural oil or artificial sweetener.
In the food applications used antibiotic preparation usually the temperature of its antibiotic effect when using raise and increase.
Process meat and meat products
Can use the known Method and Process of those skilled in the art, prepare composition of the present invention by mixing said ingredients.For example, concentrated composition is by being prepared as follows: fatty acid propylene glycol ester is heated to 70 ℃, adds surfactant, then add the reinforcing agent that is dissolved in the fatty acid ester and form solution.In some embodiments, can in the step different from applying reinforcing agent, apply antibiotic lipid.
Composition of the present invention can be used in the food process factory in various suitable modes in the different phase of processing.For example, composition of the present invention can injection, rinsing or wash solution form are coated on the meat products, such as the ox trunk, and the beef limit, Cowhells, or twist thin meat.Meat products also can be submerged in the composition.In addition, the present invention has extensively applicable temperature range, thereby allows composition to use in the different phase of processing factory.For example, composition can at high temperature use, thereby makes the sterilization of ox trunk, in the lower use of low temperature (4-5 ℃), thereby makes the thin beef of strand and the sterilization of beef limit.Composition of the present invention also can be used for United States Patent (USP) 5,460, in 833 and 5,490,992 described products and the method.
Process plant and plant part
Use preparation of the present invention, can reduce the lip-deep plant pathogeny of plant and plant part body, thereby prolong the shelf-life of plant and plant part.The unrestricted example of plant pathogeny body comprises Erwinia carotovora, Fusarium species, Botrytis species, Playtopthera species, Plaoma species, Verticilium species, Penicillium notatum species, and Colletotrichum species.Preparation of the present invention also can reduce the lip-deep spore survival of plant and plant part effectively, such as the spore of Penicillium notatum fungi.
Preparation of the present invention can be coated on plant and the plant part by for example spraying, flood, wipe examination, brushing, pat or clogging.Preparation can be coated on the part or all of outer surface of plant or plant part.In great majority were used, all surfaces of plant or plant part was by the preparation complete wetting.In some embodiments, can in the step different from applying reinforcing agent, apply antibiotic lipid.
Can under 2 ℃~90 ℃ temperature, apply preparation, and with Surface Contact long enough time of plant or plant part, to reduce bacteria levels (for example, 10 seconds~60 minutes).Usually, temperature raises, and coating time reduces.For reduce on plant or the plant part bacteria levels especially effectively, add heating agent to 40 ℃-65 ℃ (for example, 44-60 ℃, 46-58 ℃, 48-56 ℃, or 50-54 ℃), and under warm, be coated on the surface.In addition, if plant or plant part are boiled, composition so of the present invention is effective especially.If there is liquid excipient on the surface at plant or plant part, so for example can remove by the air drying.
The plant that is fit to and plant part can comprise the goods of raw material agricultural product (that is, unprocessed goods) and processing.The limiting examples of raw material agricultural product comprises alfalfa seed, bud, and cucumber, muskmelon, onion, lettuce, cabbage, carrot, potato, eggplant, citrus fruit, such as shaddock, lemon, bitter orange, and orange, banana, pineapple, Chinese gooseberry, and apple.The goods of processing comprise and tearing, and section is cut down, chopping, or fruit or the vegetables of chopping, and the juice that obtains from fruit or vegetables.
For example, fruit such as orange can be processed with antibiotic preparation of the present invention, and air is dry, then applies with food-grade wax.Obtain like this having the orange that is inserted in the antibiotic preparation between orange and the food-grade coating.Optional, antibiotic preparation and food-grade coating can be mixed before applying.In another kind was selected, food-grade wax can be applied on fruit such as the orange, then processes fruit with bactericidal composition on wax.These can the aqueous dispersion form apply easily.The wax that is fit to is beeswax, cetyl palmitate etc.
Composition of the present invention also can be used in the described goods of international publication WO 200143549A and the method.
They also can be used on food processor appliances, medical apparatus, cloth, paper or any surface that needs bactericidal activity.
Dental applications
The method that the invention provides antibiotic composition for tooth and use and make composition.This composition is used for the treatment of mouth disease by effectively reducing, prevent or eradicating the malignant bacteria species, such as carious tooth or periodontal disease.Usually, composition to the oral cavity on the hard or soft tissue, and is the composition that recovers oral hard tissue by topical application.Oral hard tissue comprises the dental structure surface, comprises tooth structure (for example, enamel, dentine, and cementum) and bone.Oral soft tissue comprises mucosal tissue, that is, and and mucous membrane.This composition can reduce effectively, prevention, or microbiological eradication, especially bacterium, fungi, and virus.In certain embodiments, composition for tooth of the present invention has broad spectrum of activity.
Some composition for tooth of the present invention provides effective local antibacterial active, therefore (comprise virus, bacterium, fungi for topical therapeutic and/or prevention because of microorganism, mycoplasma, and protozoa) on oral cavity tissue or dental material, causes or worsens the disease of generation.It should be noted that certain embodiments of the present invention have the possibility of extremely low generation microorganism patience.Therefore, this composition can apply repeatedly within one day or many days, to treat the oral surfaces infection or to eradicate undesired bacterium.In addition, composition of the present invention can carry out multiple therapeutic scheme to same patient, and does not worry producing antibiotic resistance.
Be suitable for using in the oral cavity composition for tooth of the then infection control of mouthful outer device of processing also within the scope of the invention.
Composition for tooth of the present invention comprises one or more antibiotic lipid compositions, such as the fatty acid ester of polyalcohol, and the aliphatic ether of polyalcohol, its oxyalkylated derivative etc.Fatty-acid monoester is preferred material.Preferred fatty-acid monoester comprises glyceryl monolaurate, Capmul MCM C10, Capmul MCM C8, mono laurate propylene glycol ester, single capric acid propylene glycol ester, single sad propylene glycol ester, and its combination.
Some preferred composition for tooth contains reinforcing agent or synergist, and it is selected from organic acid (for example, benzoic acid), sugar (such as wood sugar and mannose), sugar alcohol (such as xylitol), bacteriocin (such as nisin), albumen (such as lactoferrin), and its combination.Other components that can comprise are surfactant (such as dioctyl sulfo-sodium succinates), hydrophilic component (such as glycols, rudimentary alcohol ether, short-chain ester, and its combination), and hydrophobic components.Composition can use with conc forms, or is blended in water-based or the non-aqueous excipient before using.
Another aspect of the present invention is a kind of composition for tooth, is used for removing carious lesions by chemical-mechanical or by enzyme, and it can remove the carious tooth bacterium of any remnants in the affected area effectively.In some embodiments, after removing carious lesions by chemical-mechanical, by enzyme or by pure mechanical system, can apply independent bactericidal composition.
Antibiotic composition of the present invention can hydrojet, the form of washing lotion, rinsing liquid, liquid, pastel or powder is used, to reduce the concentration of the noxious bacteria in the oral cavity, for example, Streptococcus mutans.This tooth includes but not limited to oral cavity rinsing liquid (for example, mouthwass), dentilave solution, remineralization solution etc. with goods.In one aspect of the method, composition can be used for oral cavity prevention, for example, and preventative pastel, preventative powder, cleaning agent etc. under the gums.Be directly used in the structural composition of hard dentistry and comprise denfifrice (for example, toothpaste), adhesive of tooth, and etchant.
Composition of the present invention also can be used for providing antimicrobial protection to dentistry article and dental equipment, for example, the dental tooth stamper disc, dental appliance, dental floss, dental floss stick, the tooth band, tooth is with packing (for example, fiber) etc.
Make article
Preparation of the present invention can be packaged advances in the kit.Some antibiotic lipids can be inherent reactivities, particularly when having reinforcing agent.For example, fatty-acid monoester can be hydrolyzed into corresponding fatty acid in aqueous medium, with the reinforcing agent that contains hydroxyl (for example, lactic acid) ester exchange occurs, or with the solvent generation ester exchange that contains hydroxyl.The component that depends on selection, the antibacterial activity of fluid composition can be lowered, and the shelf-life can shorten to less than 1 year.
Therefore, preparation can be packaged into (kit) in two parts system easily, to improve stability.In an example of two parts system, all components of preparation except reinforcing agent, all be present in the container, and reinforcing agent is present in another container.In another example, the first container contains all components of composition, comprise the reinforcing agent that is dissolved in the fatty acid propylene glycol ester, and second container holds the second reinforcing agent.Before being coated on suitable food or the surface, the inclusion in each container is mixed to together, and can be diluted.
In some embodiments, antibiotic preparation is wrapped in the container, and this container comprises be used to the separation chamber that stores various components, for example, reinforcing agent in a chamber, antibiotic lipid and choose any one kind of them or kinds of surface activating agent and the second reinforcing agent in second chamber of this container.This two-compartment container uses frangible or displaceable spacer usually between two Room.Spacer can be broken or displacement, to mix.Optional, the structure of container does not need to mix the whole inclusions in each chamber so that the part inclusion in each chamber can be removed.Referring to, for example, United States Patent (USP) 5,862, in 949,6,045,254 and 6,089,389 for the explanation of two-compartment container.
Unless refer else, all technology used herein and scientific and technical terminology and the technical staff in the technical field of the invention the implication usually understood identical.Although can be used for implementing the present invention to described those methods similar or of equal value and material, the following describes suitable method and material.If any conflict, be as the criterion with this specification (comprising definition).In addition, material, method and embodiment only are used for illustrative, are not limited to.To further specify the present invention in the following embodiments, but be not used in the scope of the invention described in restriction claims.
Embodiment
The following examples intention gives particulars and embodiment to enforcement of the present invention.The following examples are used for explanation to help to understand the present invention, are not limited to scope of the present invention.Unless refer else, all materials are all buied commercially.Unless refer else, all umbers in an embodiment, percentage, ratio etc. all are by weight.
Nomenclature
Figure BDA0000135802060000261
Embodiment 1-4 and comparative example C1-C8: the antibiotic effect on the crust
By mixing 94 weight portion PGMC8 and 6 weight portion DOSS prepare concentrate 1.By being diluted to, concentrate 1 in the water that contains respectively mannitol or lactoferrin or nisin or colistin, is 0.5-1wt-% Preparation Example solution.The ratio of the various reinforcing agents that mix is listed in table 1 and the table 2.Agitation of solutions is until form creamy emulsion.After preparation, use immediately emulsion solution.The pH value of all final solutions is 4.5-5.Make to prepare in a like fashion comparative example, wherein do not have reinforcing agent or antibiotic lipid.
Table 1. is for the preparation w/w% of embodiment 1-3 and comparative example C1-C6
Figure BDA0000135802060000271
Table 2. is for the preparation of embodiment 4 and comparative example C7 and C8
Figure BDA0000135802060000272
Inoculum and test process:
From AOAC official method (AOAC official method 991.49,6.2.05) process, test is to the guiding sterilization functions of Pseudomonas aeruginosa, be used to test to the sterilization functions of Pseudomonas (ATCC 9027), AOAC official method 955.15: test is used to test to Methicilum Resistant Staphylococcus Aureus (MRSA) sterilization functions (ATCC#33593) to the sterilization functions of Staphylococcus aureus.Original inoculum: Pseudomonas:8.00 log unit (1 * 10 8Colony forming unit (CFU)/milliliter (mL)); MRSA 8 log units (1 * 10 8CFU/mL).
In this test, apply hollow glass cylinder (penicylinder) with the tested person bacterium.Bacterium is dry 1 hour (hr) on penicylinder.The penicylinder that will contain dry bacterium flood 24 hours in the embodiment preparation, and then taking-up, and place neutralization solution (D/E and meat soup) to reach 30 seconds puts in the glass tube that contains tryptic soy broth (TSB) 24 hours into.After 24 hours, analyze the turbidity of the pipe that contains penicylinder, be designated as growth or not growth.10 hollow glass cylinders of every kind of preparation test.If 0 pipe shows not growth in 10 pipes, preparation is classified work " qualified " so.If 1 pipe shows growth in 10 pipes, preparation is classified work " defective " so.
The antibiotic preparation effect of table 3. couple Pseudomorzas (ATCC 9027)
Figure BDA0000135802060000281
Table 4. couple MRSA (ATCC#; 33593) antibiotic preparation effect
Table 4 Comparative example C7 Comparative example C8 Embodiment 4
Preparation 11 Preparation 12 Preparation 13
Defective pipe/house steward 2/10 3/10 0/10
Grade Defective Defective Qualified
Embodiment 5-7 and comparative example C9-C10: process the thin beef of strand
The extra reinforcing agent that uses lactoferrin and nisin to process as the thin beef of strand is analyzed antibiotic effect.
Measure the natural bacteria counting on the thin beef of strand
Buy the thin beef of strand from food supply retail shop, by the thin beef of 11-gram (11-g) strand is placed with 99 milliliters of (mL) Letheen meat soup (VWR Scientific, Batavia, IL) among the independent homogenizer bag #6469 (3M, St.Paul, MN) that filters, and at laboratory stirring Stomacher 400 (Tekmar, Cincinnati, OH) middle digestion 1 minute, test immediately natural count of bacteria.The dilution for preparing 10 times of serial dilutions with Letheen meat soup.Sample is layered on PETRIFILM Enterobacteriaceae tally (EB) (from 3M, St.Paul, MN obtains) and PETRIFILM Aerobic counting (AC) plate (from 3M, St.Paul, MN obtains).The PETRIFILM plate is hatched 24+/-2 hour under 35 ℃, by counting of recommending on the packing insert.Use the tally of the range of readings interior (25-250 CFU/PETRIFILM AC plate and 15-100 CFU/PETRIFILMEB plate) of plate to analyze.
Preparation preparation and meat are processed
By the listed component of following table 5 is added in the glass container, prepare the concentrate (concentrate 2) of antibiotic lipid.Container is heated to 50-80 ℃ at heating plate, in heating process, continues agitating solution (by magnetic stirring apparatus or dasher).Mixed solution is until obtain the single-phase liquid of homogeneous transparent.Use this concentrate to process the thin beef sample of strand.
Table 5 Concentrate 2
GML12 15.0
PGMC8 45.0
Pationic 122A 10.0
Span 20 15.0
DOSS 3.0
BHA 2.0
Benzoic acid 10.0
Process the thin beef sample of strand with two parts system (part A and part B).Part A is comprised of the concentrate 2 that is diluted to 40wt-% in water, and part B is by by dissolving 10wt-% lactoferrin or 1.6wt-% nisin in water or dissolving 10wt-% lactoferrin and 1.6wt-% nisin obtain in water reinforcing agent solution composition.
The thin beef of the strand that claimed weight is added in the KITCHEN-AID blender that oar formula mixing head is installed.Part B solution is placed the pressure cooker (23 ℃) that is connected with nozzle.Solution is ejected in the thin beef of strand contained in the blender (5 ℃), mixes with arm mixer simultaneously.The meat that sprays contains the aqueous solution of the 2.5wt-% that has an appointment.In 1.5 minutes (min), 0.25wt-% lactoferrin and/or 0.04wt-% nisin (800IU) are transported in the thin beef of strand like this.Then use part A (40wt-% concentrate 2) to spray sample.The meat that sprays contains the 2.5wt-% aqueous solution of having an appointment (1wt-% concentrate 2 is transported in the meat sample).Total incorporation time is 3 minutes.The thin beef sample of strand of processing is placed refrigerator again.Use above-mentioned course of injection, the thin meat of pair twist carries out five groups of processing.After spraying and mixing, in the table 6 below the final percentage after each the processing in meat is listed in.
Table 6. is for embodiment 5-7 and comparative example 9﹠amp; 10, the final component percentages in the meat
Figure BDA0000135802060000301
In the preservation process, these samples do not have change color.After 24 hours, the 11-g that weighs twists thin beef, and places the homogenizer bag that filters with 99mL Letheen meat soup, obtains the sample bag.Digested 30 seconds of sample in the bag is to help from meat except degerming.By 1mL being transferred in the 9mL Letheen meat soup 10 times of the solution of serial dilution digestion.Use PETRIFILMAC and PETRIFILM EB as medium, analyze the solution of every kind of dilution.Use the tally of the range of readings interior (25-250 CFU/PETRIFILM AC plate and 15-100 CFU/PETRIFILM EB plate) of plate to analyze.The result changes into log unit 10, the on average value of copying.From similar untreated meat sample result, deduct the meat sample result of processing, measure the log unit of processing and reduce.Table 7 shows the data that obtain from above-mentioned test.
Figure BDA0000135802060000311
Criticize meat with difference and repeat identical experiment 3 times, observe similar result.Embodiment in the table 7 shows, under 4 ℃, is twisting on the thin beef, and three kinds of reinforcing agents (carboxylic acid, bacteriocin, iron-binding protein) all provide obvious antibiotic effect.Expection can prolong the shelf-life of meat like this, and can not affect organoleptic properties.
Embodiment 8
Repeat embodiment 5, the difference below noting.Use is with the pressurized jet device (Sprayer Systems Co., Wheaton, IL) of fan nozzle.Arrange down in low the mixing, use with the KITCHEN-AID blender mixing portion A (undiluted) of oar formula annex and part B (containing lactoferrin and nisin) 3 minutes.At first in 1.5 minutes of mixing, with the injection rate of 30mL/min, carry reinforcing agent (part B).In this case, part A (concentrate 2) is not diluted, and carries with the injection rate of 7.5mL/min, continues simultaneously to mix 1.5 minutes (min).Add capacity reinforcing agent and antibiotic lipid, so that the concentrate 2 of 1wt-% and the reinforcing agent solution of 4wt-% are transported to meat.Initial natural bacteria is the 40-80counts/ gram, detects with PETRIFILM AC.Process after 10 minutes, can not detect natural bacteria.
Embodiment 9-28 and comparative example C11-C15
By mixture table 8 and 9 listed components, preparation antibacterial liquid composition (embodiment 9-28 and comparative example C11-C15), they might be used for people's oral cavity.Every kind of fluid composition contains the water (containing 0.5wt-%PLURONIC P65 surfactant) as dicyandiamide solution, two kinds of fatty-acid monoesters (PGMC8 and GMLC12), anion surfactant (DOSS), optional organic acid reinforcing agent (benzoic acid), with be selected from sucrose, xylitol, lactoferrin, and the reinforcing agent of nisin.There is not the composition (that is, the organic acid reinforcing agent only being arranged) of the second reinforcing agent (to represent with letter C) in contrast.
Figure BDA0000135802060000321
Figure BDA0000135802060000331
Analyze and the result
Kill the rate test method according to following antibiotic (Streptococcus mutans), analyze the antibacterial activity of bactericidal composition (embodiment 9-28 and comparative example C11-C15).The results are shown in Table 10.
Antibiotic (Streptococcus mutans) kills the rate test method
Under the given concentration in water, will be in brain heart infusion (BHI) meat soup 10 8The sample of the 0.1mL S.mutans (ATCC#25175) of CFU/ml and the antibiotic sample mix scheduled time of 19.9mL liquid testing (0.5 minute, 2 minutes, 5 minutes, and 10 minutes).After mixing the scheduled time, immediately the 1.0mL sample is transferred to from flask in the testing tube that contains 9.0mL Letheen meat soup (VWR Scientific, Batavia, IL), in order to fatty-acid monoester and the benzoic acid component that may in sample, exist.Use vortex mixer fully to mix, the solution that obtains is called 10 -1Dilution.With the 1.0-mL sample from 10 -1Dilution is transferred in the second pipe that contains 9.0mL Letheen meat soup, and by above-mentioned mixing, obtains solution, is called 10 -2Dilution.Every kind 10 -1With 10 -2The sample of dilution (0.1mL) repeats bed board, and uses the Blood In Sheep agar of hockey stick applicator on Petri vessel plate to launch, and the concentration on each plate is 10 -2With 10 -3The Petri vessel were hatched 96 hours under 37 ℃ of aerobic conditions, then counted the quantity of colony forming unit (CFU).Under the certain concentration of specimen, this information is used to calculate the speed of killing of S.mutans.
Figure BDA0000135802060000351
Can release from table 10, usually, the bactericidal composition that contains organic acid reinforcing agent (benzoic acid) reduces with the S.mutans log unit that the bactericidal composition that contains organic acid reinforcing agent and reinforcing agent shows maximum horizontal.
Obviously, those skilled in the art can make various modifications and variations within the spirit and scope of the present invention.Should be appreciated that, the present invention is not intended to limit in exemplary embodiment and embodiment, and this embodiment and embodiment only are used for illustrating scope of the present invention, and scope of the present invention is only limited by claims.

Claims (3)

1. bactericidal composition comprises:
Antibiotic lipid composition, it comprises the compound of aliphatic ether, its oxyalkylated derivative and its combination of the fatty acid ester that is selected from polyalcohol, polyalcohol; Wherein oxyalkylated derivative has less than 5 moles of alkoxide/mole polyalcohol; Condition is that described antibiotic lipid does not comprise monoglyceride; With
Enhancer component, it comprises at least two kinds reinforcing agent at least two kinds of inhomogeneity compounds, wherein at least a reinforcing agent is the compound that is selected from mannose, wood sugar, mannitol, xylitol and its combination; With
Surfactant, it is selected from cation, anion, nonionic, amphoteric surfactant and its combination, wherein non-ionic surface active agent is selected from glyceride, sorbitol ester, the block copolymer of polyalkylene oxide and its combination;
Wherein said composition has antibacterial activity.
2. bactericidal composition comprises:
Antibiotic lipid composition, it comprises the compound of aliphatic ether, its oxyalkylated derivative and its combination of the fatty acid ester that is selected from polyalcohol, polyalcohol;
Wherein the formula of the fatty acid ester of polyalcohol is (R 1-C (O)-O) n-R 2, R wherein 1(C7-C14) saturated fatty acid or (C8-C22) residue of unsaturated fatty acid, R 2Be glycerine, the residue of propane diols or sucrose is worked as R 2N=1 when being the residue of glycerine or propane diols, and work as R 2N=1 or 2 when being the residue of sucrose; With
Enhancer component, it comprises at least two kinds reinforcing agent at least two kinds of inhomogeneity compounds, wherein at least a reinforcing agent is organic acid, and at least a reinforcing agent is the compound that is selected from bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore and its combination; With
Surfactant, it is selected from cation, anion, nonionic, amphoteric surfactant and its combination, wherein non-ionic surface active agent is selected from glyceride, sorbitol ester, the block copolymer of polyalkylene oxide and its combination;
Wherein said composition has antibacterial activity.
3. bactericidal composition comprises:
Antibiotic lipid composition, it comprises the compound of aliphatic ether, its oxyalkylated derivative and its combination of the fatty acid ester that is selected from polyalcohol, polyalcohol;
Wherein the formula of the fatty acid ester of polyalcohol is (R 1-C (O)-O) n-R 2, R wherein 1(C7-C14) saturated fatty acid or (C8-C22) residue of unsaturated fatty acid, R 2Be glycerine, the residue of propane diols or sucrose is worked as R 2N=1 when being the residue of glycerine or propane diols, and work as R 2N=1 or 2 when being the residue of sucrose; With
Enhancer component, it comprises at least two kinds reinforcing agent at least two kinds of inhomogeneity compounds, wherein at least a reinforcing agent is organic acid, chelating agent or phenolic compound, and at least a reinforcing agent is the compound that is selected from bacteriocin, antibiotic enzyme, sugar, sugar alcohol, iron-binding protein and its derivative, siderophore and its combination; With
Surfactant, it is selected from cation, anion, nonionic, amphoteric surfactant and its combination, wherein non-ionic surface active agent is selected from glyceride, sorbitol ester, the block copolymer of polyalkylene oxide and its combination;
Wherein said composition has antibacterial activity.
CN2012100341505A 2003-09-09 2004-09-08 Antimicrobial compositions and methods Pending CN102845422A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US50181703P 2003-09-09 2003-09-09
US60/501,817 2003-09-09

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CNA200480029760XA Division CN1867251A (en) 2003-09-09 2004-09-08 Antimicrobial compositions and methods

Publications (1)

Publication Number Publication Date
CN102845422A true CN102845422A (en) 2013-01-02

Family

ID=34273070

Family Applications (2)

Application Number Title Priority Date Filing Date
CN2012100341505A Pending CN102845422A (en) 2003-09-09 2004-09-08 Antimicrobial compositions and methods
CNA200480029760XA Pending CN1867251A (en) 2003-09-09 2004-09-08 Antimicrobial compositions and methods

Family Applications After (1)

Application Number Title Priority Date Filing Date
CNA200480029760XA Pending CN1867251A (en) 2003-09-09 2004-09-08 Antimicrobial compositions and methods

Country Status (11)

Country Link
US (2) US20050053593A1 (en)
EP (1) EP1662873B1 (en)
JP (1) JP2007505125A (en)
KR (1) KR20060095756A (en)
CN (2) CN102845422A (en)
AU (2) AU2004270258A1 (en)
BR (1) BRPI0414193A (en)
CA (1) CA2538103A1 (en)
MX (1) MXPA06002719A (en)
WO (1) WO2005022998A2 (en)
ZA (1) ZA200602885B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105611909A (en) * 2013-03-12 2016-05-25 艾米丽·A·斯坦 Dental composition comprising chelating agent and base
CN107709349A (en) * 2015-05-20 2018-02-16 阿比尔技术公司 Composition of plant extracts and the method for preparing it
CN109512998A (en) * 2016-03-04 2019-03-26 广州英赛特生物技术有限公司 The application of synergetic effect additive of the esterification derivative of oxygen-containing hydrocarbon derivative as polymyxins
US11028030B2 (en) 2015-12-10 2021-06-08 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US11319275B2 (en) 2016-11-17 2022-05-03 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof

Families Citing this family (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100534334C (en) * 2003-09-09 2009-09-02 3M创新有限公司 Concentrated antimicrobial compositions and methods
US20050058673A1 (en) * 2003-09-09 2005-03-17 3M Innovative Properties Company Antimicrobial compositions and methods
US7592159B2 (en) * 2004-03-15 2009-09-22 Iowa State University Research Foundation, Inc. Antibiotic alternatives
US9028852B2 (en) 2004-09-07 2015-05-12 3M Innovative Properties Company Cationic antiseptic compositions and methods of use
CN101137359B (en) * 2005-03-10 2011-01-12 3M创新有限公司 Methods of treating ear infections
BRPI0608690B8 (en) * 2005-03-10 2021-05-25 3M Innovative Properties Co use of an antimicrobial composition
MX2007010904A (en) * 2005-03-10 2007-12-05 3M Innovative Properties Co Antimicrobial pet wipes and methods.
US20060205838A1 (en) * 2005-03-10 2006-09-14 Velamakanni Bhaskar V Hardenable antimicrobial dental compositions and methods
EP1898900B1 (en) 2005-03-10 2011-06-08 3M Innovative Properties Company Antimicrobial compositions comprising esters of hydroxycarboxylic acids
US20060204452A1 (en) * 2005-03-10 2006-09-14 Velamakanni Bhaskar V Antimicrobial film-forming dental compositions and methods
US20100080790A1 (en) * 2005-07-13 2010-04-01 University Of South Carolina Sterilization using high-pressure carbon dioxide
WO2007024867A2 (en) * 2005-08-23 2007-03-01 3M Innovative Properties Company Methods of applying antimicrobial formulations on food
US20070048345A1 (en) * 2005-08-31 2007-03-01 Kimberly-Clark Worldwide, Inc. Antimicrobial composition
EP1968627B1 (en) * 2005-11-18 2014-12-10 Glanbia Nutritionals (Ireland) Limited Compositions for disrupting and inhibiting reconstitution of wound biofilm
WO2008140862A1 (en) * 2007-05-08 2008-11-20 Biotechnology Research And Development Corporation Optimization of colicin production
US8119688B2 (en) * 2007-09-19 2012-02-21 Xy, Llc Differential evaporation potentiated disinfectant system
CN101951887B (en) * 2007-12-31 2013-03-13 3M创新有限公司 Liquid antiseptic compositions containing iodine and a sugar and/or sugar alcohol
EP2082739A1 (en) 2008-01-25 2009-07-29 PURAC Biochem BV Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals
US7842725B2 (en) 2008-07-24 2010-11-30 Ecolab USA, Inc. Foaming alcohol compositions with selected dimethicone surfactants
IT1393045B1 (en) * 2009-03-16 2012-04-11 Cantini COMPOSITIONS CONTAINING MONOGLICERIDES OF ORGANIC ACIDS FROM C1 TO C7 AND GLYCEROL, THEIR PREPARATION AND USE AS ANTIBACTERIALS IN THE ZOOTECHNY.
FR2945180B1 (en) 2009-05-07 2013-02-22 Arjowiggins Security INFORMATION CARRIER HAVING ANTIVIRAL PROPERTIES AND METHOD FOR MANUFACTURING THE SAME
EP2427184B1 (en) 2009-05-08 2017-08-30 3M Innovative Properties Company Oral care method and kit
EP2461700B1 (en) * 2009-08-06 2016-04-20 Anitox Corporation Water and feed preservative
FR2967074B1 (en) 2010-11-08 2013-06-28 Arjowiggins Security FLUID COMPOSITIONS CAPABLE OF FORMING A COATING HAVING ANTIVIRAL PROPERTIES
KR101381903B1 (en) * 2011-03-10 2014-04-10 주식회사 엘지생활건강 Antibacterial or preservative composition containing 3-butoxy-1,2-propanediol
US20120237641A1 (en) * 2011-03-15 2012-09-20 Tiandong Jia Pet food coating for reducing dental calculus accumulation in domestic animals
JP5845603B2 (en) * 2011-03-18 2016-01-20 ライオン株式会社 Liquid or liquid oral composition and tongue coating adhesion inhibitor
EP2785205B1 (en) 2011-11-30 2020-12-30 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and organic acid esters
WO2013081626A1 (en) 2011-12-02 2013-06-06 Colgate-Palmolive Company Oral care composition comprising isobutyl magnolol
US9642362B2 (en) 2012-04-16 2017-05-09 Cascades Canada Ulc Antimicrobial compositions and uses thereof
EP2854756B1 (en) * 2012-06-05 2021-10-06 Amity Capital Limited Temporary stain repellent for preventing staining of teeth
JP6150271B2 (en) * 2012-11-01 2017-06-21 理研ビタミン株式会社 Bacteriostatic agent for oral aerobic bacteria
JP6149252B2 (en) * 2012-11-01 2017-06-21 理研ビタミン株式会社 Bacteriostatic agent for oral anaerobic bacteria
CN102939966B (en) * 2012-11-08 2016-01-13 北京大北农动物保健科技有限责任公司 A kind of compound disinfectant, its preparation method and application
US20150373970A1 (en) * 2013-02-04 2015-12-31 3M Innovative Properties Company Antimicrobial compositions, wipes, and methods
US9573980B2 (en) 2013-03-15 2017-02-21 Spogen Biotech Inc. Fusion proteins and methods for stimulating plant growth, protecting plants from pathogens, and immobilizing Bacillus spores on plant roots
KR101473925B1 (en) * 2013-05-16 2014-12-22 (주)에이씨티 Antiseptic compositions comprising Magnolia grandiflora extract and cosmetic compositions containing the same
US9744542B2 (en) 2013-07-29 2017-08-29 Apeel Technology, Inc. Agricultural skin grafting
CN105530926B (en) 2013-09-13 2019-07-16 3M创新有限公司 Cationic preservative composition
CN108135188B (en) 2015-09-16 2022-08-05 阿比尔技术公司 Precursor compounds for molecular coatings
CN105309478A (en) * 2015-12-14 2016-02-10 广西大学 Ustilaginoidea virens inhibitor from xylose
CN105360165A (en) * 2015-12-14 2016-03-02 广西大学 Preparation method of ustilaginoidea virens (Cooke) Takahashi inhibitor prepared from potato-xylose
CN105340996A (en) * 2015-12-14 2016-02-24 广西大学 Ustilaginoidea virens inhibitor derived from potato-xylose mixture
CN105325459A (en) * 2015-12-14 2016-02-17 广西大学 Preparation method of rice germ inhibitor coming from xylose
EP3398996B1 (en) * 2015-12-28 2021-01-27 Sumitomo Chemical Company, Limited Composition
JP6913110B2 (en) 2016-01-26 2021-08-04 アピール テクノロジー,インコーポレイテッド Methods for preparing and storing sanitized products
WO2017192417A1 (en) * 2016-05-04 2017-11-09 3M Innovative Properties Company Enzymatic cleaning compositions and methods
AU2019212769B2 (en) * 2018-01-23 2021-06-17 Greening Be Gone, LLC Method of treating citrus greening
US10624368B1 (en) * 2018-02-01 2020-04-21 Nevada Naturals Inc. Control of pathogenic bacteria in foods
CN112469281B (en) * 2018-05-15 2023-05-30 旗舰创业创新六公司 Pest control composition and use thereof
US12245605B2 (en) 2018-09-05 2025-03-11 Apeel Technology, Inc. Compounds and formulations for protective coatings
EP3905985A4 (en) * 2018-12-31 2022-08-31 3M Innovative Properties Company Antimicrobial dental appliance
WO2020229202A1 (en) 2019-05-15 2020-11-19 Purac Biochem B.V. Lactylate blend for preservative/antimicrobial system
JP7578707B2 (en) 2020-03-04 2024-11-06 アピール テクノロジー,インコーポレイテッド Coated agricultural products and corresponding methods
WO2022010893A1 (en) 2020-07-06 2022-01-13 Ecolab Usa Inc. Foaming mixed alcohol/water compositions comprising a combination of alkyl siloxane and a hydrotrope/solubilizer
WO2022010906A1 (en) 2020-07-06 2022-01-13 Ecolab Usa Inc. Peg-modified castor oil based compositions for microemulsifying and removing multiple oily soils
MX2023004343A (en) 2020-10-30 2023-05-08 Apeel Tech Inc Compositions and methods of preparation thereof.
US20250127740A1 (en) * 2021-11-09 2025-04-24 Arizona Board Of Regents On Behalf Of The University Of Arizona Composition containing 3-hydroxyanthranilic acid and compounds that alter iron homeostasis and method of its use
WO2024187054A1 (en) * 2023-03-07 2024-09-12 Onyx Lotus, Llc Compositions and methods for producing a food contact safe antimicrobial composition containing an essential oil complex
KR102604612B1 (en) * 2023-03-07 2023-11-22 주식회사 일신웰스 Hand sanitizer composition with excellent antibacterial durability

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05229915A (en) * 1992-02-24 1993-09-07 Kanebo Ltd Skin external preparation
EP0629347A1 (en) * 1992-01-23 1994-12-21 Morinaga Milk Industry Co., Ltd. Antibacterial agent and treatment of article therewith
CN1172615A (en) * 1996-07-01 1998-02-11 三菱化学食品株式会社 Anti-bacteria agent
CN1313086A (en) * 2000-02-15 2001-09-19 欧莱雅 Use of fatty materials for prevention or reduction of microorganism adhere on skin and/or mucous membrane

Family Cites Families (105)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE615683A (en) * 1961-03-29
US3489148A (en) * 1966-12-20 1970-01-13 Procter & Gamble Topsheet for disposable diapers
US3806615A (en) * 1970-06-03 1974-04-23 Exxon Research Engineering Co Aliphatic diols and their esters as antimicrobial additives for cheese and meats
US3983214A (en) * 1972-12-08 1976-09-28 Ajinomoto Co., Inc. Fungicidal compositions and method for protecting plants by the use thereof
JPS5132701B2 (en) * 1973-06-29 1976-09-14
US4002775A (en) * 1973-07-09 1977-01-11 Kabara Jon J Fatty acids and derivatives of antimicrobial agents
US4067997A (en) * 1975-05-21 1978-01-10 Med-Chem Laboratories Synergistic microbecidal composition and method
US4189481A (en) * 1975-11-18 1980-02-19 Michigan State University Antimicrobial compositions
US4168323A (en) * 1976-06-01 1979-09-18 Kabushiki Kaisha Veno Seiyako Oyo Kenkyujo Food additive composition and process for preparation thereof
GB1593856A (en) * 1976-11-17 1981-07-22 Gist Brocades Nv Process for the treatment of fruit and vegetables
US4113854A (en) * 1977-01-10 1978-09-12 Minnesota Mining And Manufacturing Company Prophylactic treatment of mastitis
US4160820A (en) * 1977-11-28 1979-07-10 General Mills, Inc. Plaque inhibiting composition and method
US4722941A (en) * 1978-06-07 1988-02-02 Kali-Chemie Pharma Gmbh Readily absorbable pharmaceutical compositions of per se poorly absorbable pharmacologically active agents and preparation thereof
JPS5511556A (en) * 1978-07-13 1980-01-26 Rikagaku Kenkyusho Bactericidal agent for agriculture and horticulture
US4284653A (en) * 1979-01-13 1981-08-18 Nippon Suisan Kabushiki Kaisha Process for handling and processing fish meat
KR830005852A (en) * 1980-07-18 1983-09-14 미첼 페터 잭슨 Preparation of topical treatments suitable for the treatment of viral infections on skin and mucous membranes
US4530963A (en) * 1982-08-20 1985-07-23 Devoe-Holbein International, N.V. Insoluble chelating compositions
US4648876A (en) * 1982-09-24 1987-03-10 Personal Products Company Breathable panty liner
GB2187929B (en) * 1985-05-29 1989-07-12 Mo T I Myasnoj Moloch Promy Method of preparing and preserving balyk
DE3682908D1 (en) * 1985-09-24 1992-01-23 Ss Pharmaceutical Co FUNGICIDE AGENT.
US5208257A (en) * 1986-04-21 1993-05-04 Kabara Jon J Topical antimicrobial pharmaceutical compositions and methods
AU618517B2 (en) * 1986-12-23 1992-01-02 Eugene J. Van Scott Additives enhancing topical actions of therapeutic agents
US5225473A (en) * 1987-11-25 1993-07-06 Minnesota Mining And Manufacturing Company Pressure-sensitive adhesives
US4931282A (en) * 1987-11-25 1990-06-05 Minnesota Mining And Manufacturing Company Pressure-sensitive medical sealant
US5434182A (en) * 1987-12-31 1995-07-18 Isaacs; Charles E. Antibacterial fatty acid compositions
US4997851A (en) * 1987-12-31 1991-03-05 Isaacs Charles E Antiviral and antibacterial activity of fatty acids and monoglycerides
US4840738A (en) * 1988-02-25 1989-06-20 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts
US5231087A (en) * 1988-03-16 1993-07-27 Cellegy Pharmaceuticals, Inc. Treatment of skin diseases and tumors with esters and amides of monocarboxylic acids
US5304540A (en) * 1988-06-22 1994-04-19 Applied Microbiology, Inc. Pharmaceutical bacteriocin compositions and methods for using the same
US5217950A (en) * 1988-06-22 1993-06-08 Applied Microbiology, Inc. Nisin compositions for use as enhanced, broad range bactericides
US5334582A (en) * 1988-06-22 1994-08-02 Applied Microbiology, Inc. Pharmaceutical bacteriocin compositions and methods for using the same
US5135910A (en) * 1988-06-22 1992-08-04 The Public Health Research Institute Of The City Of New York Nisin compositions for use as enhanced, broad range bactericides
US5093140A (en) * 1988-07-20 1992-03-03 Eisai Co., Ltd. Aqueous bactericide for animal treatment
US5424059A (en) * 1988-12-29 1995-06-13 Colgate Palmolive Company Antibacterial antiplaque dentifrice
US5318955A (en) * 1989-04-07 1994-06-07 Henkel Kommanditgesellschaft Auf Aktien Use of selected ethers of monofunctional alcohols in drilling fluids
US5641503A (en) * 1989-04-27 1997-06-24 Mcneil-Ppc, Inc. Additives to tampons
US4983394A (en) * 1990-05-03 1991-01-08 Warner-Lambert Company Flavor enhancing and medicinal taste masking agent
US5098694A (en) * 1990-09-25 1992-03-24 The Procter & Gamble Company Natural deodorant compositions
NZ264247A (en) * 1990-10-30 1996-07-26 Mcneil Ppc Inc Absorbent product containing mono- or diesters of a polyhydric alcohol and a c8-18 fatty acid having at least one free hydroxyl group in sufficient amount to inhibit the production of enterotoxins a, b and c by staph. aureus
US5346724A (en) * 1991-04-12 1994-09-13 Nippon Oil Company, Ltd. Oil and fat composition for lubricating food processing machines and use thereof
US5234719A (en) * 1991-06-04 1993-08-10 Ecolab Inc. Food additive sanitizing compositions
US5219887A (en) * 1991-06-07 1993-06-15 Minnesota Mining And Manufacturing Company Disinfecting shampoo composition for animals
US5378731A (en) * 1991-06-07 1995-01-03 Minnesota Mining And Manufacturing Company Medicated shampoo
DE4140473C2 (en) * 1991-12-09 1995-12-21 Schuelke & Mayr Gmbh Skin antiseptic and hand sanitizer
JP3261174B2 (en) * 1992-01-23 2002-02-25 森永乳業株式会社 Antimicrobial agent and method of treating articles using this antimicrobial agent
SE500777C2 (en) * 1992-04-14 1994-08-29 Hydro Pharma Ab Antimicrobial composition with potentiated effect containing, inter alia, certain monoglycerides, process for their preparation and their use
US5320772A (en) * 1992-05-18 1994-06-14 Empire Products Packaging Development, Inc. Composition for cleaning fruits and vegetables
JP3040282B2 (en) * 1993-07-30 2000-05-15 アサマ化成株式会社 Food preservatives
CN1128955A (en) * 1993-08-10 1996-08-14 藤泽药品工业株式会社 Percutaneously absorbable prepn.
AU692478B2 (en) * 1993-09-14 1998-06-11 Minnesota Mining And Manufacturing Company Disinfectant composition
US6228383B1 (en) * 1994-03-03 2001-05-08 Gs Development Ab Use of fatty acid esters as bioadhesive substances
WO1995026715A2 (en) * 1994-03-30 1995-10-12 Dumex-Alpharma A/S Use of fatty acid esters as bioadhesive substances
DK170962B1 (en) * 1994-04-25 1996-04-09 Danisco Coating composition and use thereof for coating cheese
US5547677A (en) * 1994-05-20 1996-08-20 Novavax, Inc. Antimicrobial oil-in-water emulsions
US5549901A (en) * 1994-05-20 1996-08-27 Novavax, Inc. Antimicrobial oil-in-water emulsions
JPH0856631A (en) * 1994-08-24 1996-03-05 Dai Ichi Kogyo Seiyaku Co Ltd Microorganism separating detergent composition for food
US5660842A (en) * 1994-10-04 1997-08-26 Bristol-Myers Squibb Company Inhibition of helicobacter
DE4438588A1 (en) * 1994-10-28 1996-05-02 Beiersdorf Ag Against blemished skin, mild forms of acne and Propionibacterium acnes active ingredient combinations based on wool wax acids and glycerol esters of saturated fatty acids
FR2729050A1 (en) * 1995-02-23 1996-07-12 Oreal Synergistic compsn. with microbicidal properties
US5736178A (en) * 1995-05-02 1998-04-07 Opta Food Ingredients, Inc. Colloidal dispersions of gluten, method of making and use therefor
FR2734158B1 (en) * 1995-05-17 1997-06-27 Roche Posay Lab Pharma COMBINATION OF A COMPOUND WITH ANTI-MICROBIAL ACTIVITY AND A MONOALKYLETHER OF GLYCEROL
US5762948A (en) * 1995-06-07 1998-06-09 Ambi Inc. Moist bacteriocin disinfectant wipes and methods of using the same
EP1374847A1 (en) * 1995-06-22 2004-01-02 Minnesota Mining And Manufacturing Company Stable hydroalcoholic compositions
EP0758641B1 (en) * 1995-08-11 2000-08-30 Daicel Chemical Industries, Ltd. A fatty acid esters composition of a polyglycerine, a process for the preparation thereof, a process for the preparation of a highly-purified fatty acid esters composition of a polyglycerine, a highly-purified fatty acid esters composition of a polyglycerine, an additive for food-stuffs, a resin composition, and a composition for cosmetics or detergents
US5906814A (en) * 1995-12-07 1999-05-25 The Andrew Jergens Company Topical film-forming compositions
AU705320B2 (en) * 1995-12-28 1999-05-20 Welfide Corporation 2-amino-2-(2-(4-octylphenyl)ethyl)propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof for use in the preparation of a non-oral medicament, and for treatment of diseases and disorders
US5804549A (en) * 1996-01-05 1998-09-08 Ambi Inc. Compositions with activity against helicobacter
ES2205217T3 (en) * 1996-05-10 2004-05-01 Johnsondiversey, Inc. CLEANING AND / OR DISINFECTING COMPOSITION.
NL1003524C2 (en) * 1996-07-05 1998-01-12 Cooperatie Cosun U A Diaper rash prevention or treatment composition.
US5862949A (en) * 1996-09-27 1999-01-26 Lever Brothers Company, Division Of Conopco, Inc. Dual container and individual chamber therefor
DE19642127A1 (en) * 1996-10-12 1998-04-16 Degussa Disinfectant containing iron-free siderophore and active oxygen compound,
US6089389A (en) * 1996-12-26 2000-07-18 M.L.I.S. Projects Ltd. Two-compartment container and method of preparing the same
US6045254A (en) * 1996-12-26 2000-04-04 M.L.I.S. Projects Ltd. Container having two or more compartments
PT977912E (en) * 1997-05-02 2005-02-28 Cargill Inc DEGRADABLE POLYMER FIBERS; PREPARATION; PRODUCT; AND METHODS OF USE
US6190675B1 (en) * 1997-06-04 2001-02-20 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide improved residual benefit versus gram positive bacteria
US6197315B1 (en) * 1997-06-04 2001-03-06 Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus gram negative bacteria
US6183763B1 (en) * 1997-06-04 2001-02-06 Procter & Gamble Company Antimicrobial wipes which provide improved immediate germ reduction
US6258368B1 (en) * 1997-06-04 2001-07-10 The Procter & Gamble Company Antimicrobial wipes
US6190674B1 (en) * 1997-06-04 2001-02-20 Procter & Gamble Company Liquid antimicrobial cleansing compositions
CN1262615A (en) * 1997-06-04 2000-08-09 普罗克特和甘保尔公司 Mild, rinse-off antimicrobial liquid cleansing compositions containing acidic surfactants
AU7706698A (en) * 1997-06-04 1998-12-21 Procter & Gamble Company, The Mild, rinse-off antimicrobial liquid cleansing compositions containing salicylicacid
US6183757B1 (en) * 1997-06-04 2001-02-06 Procter & Gamble Company Mild, rinse-off antimicrobial cleansing compositions which provide improved immediate germ reduction during washing
KR20010013377A (en) * 1997-06-04 2001-02-26 데이비드 엠 모이어 Mild, leave-on antimicrobial compositions
US6057274A (en) * 1997-08-22 2000-05-02 Henkel Corporation Antibacterial composition having enhanced tactile properties
AU9311098A (en) * 1997-09-11 1999-03-29 Brigham And Women's Hospital Absorbent article, particularly a tampon having additives that reduce toxic shock syndrome toxin production
BR9814615A (en) * 1997-10-22 2001-10-16 Jens Ponikau Methods and materials for the treatment and prevention of mucosal tissue inflammation
US6110516A (en) * 1997-11-13 2000-08-29 University Of Delaware Process for treating foods using saccharide esters and superatmospheric hydrostatic pressure
CN1321573C (en) * 1998-03-12 2007-06-20 王子制纸株式会社 Bactericides
US6033705A (en) * 1998-07-08 2000-03-07 Isaacs; Charles E. Method for treating foodstuffs to reduce or prevent microbial activity
NZ512287A (en) * 1998-12-11 2002-12-20 Pharmasolutions Inc Pharmaceutical compositions comprising a lipophilic drug in a propylene glycol ester of a higher fatty acid carrier, where 60% of the ester is a monoester
US6559189B2 (en) * 1999-04-28 2003-05-06 Regents Of The University Of Michigan Non-toxic antimicrobial compositions and methods of use
US7767216B2 (en) * 1999-04-28 2010-08-03 The Regents Of The University Of Michigan Antimicrobial compositions and methods of use
EP1178850B1 (en) * 1999-05-21 2003-10-29 3M Innovative Properties Company Antimicrobial articles
US6211243B1 (en) * 1999-09-22 2001-04-03 B. Ron Johnson Methods for treating cold sores with anti-infective compositions
US8173709B2 (en) * 1999-09-22 2012-05-08 Quadex Pharmaceuticals, Llc Anti-infective methods for treating pathogen-induced disordered tissues
US6080394A (en) * 1999-11-08 2000-06-27 Dow Corning Corporation Polar solvent-in-oil emulsions and multiple emulsions
BR0015806A (en) * 1999-11-24 2003-07-15 3M Innovative Properties Co Antimicrobial Formulation, Method for Reducing Microbial Levels in Plants or Plant Parts, Assembly, Manufacturing Article, and, Plant or Plant Part
WO2001072262A2 (en) * 2000-03-27 2001-10-04 Schott Glas New cosmetic, personal care, cleaning agent, and nutritional supplement compositions comprising bioactive glass and methods of making and using the same
US6951642B2 (en) * 2001-09-28 2005-10-04 3M Innovative Properties Company Water-in-oil emulsions with anionic groups, compositions, and methods
US7030203B2 (en) * 2001-09-28 2006-04-18 3M Innovative Properties Company Water-in-oil emulsions with ethylene oxide groups, compositions, and methods
US6943197B2 (en) * 2002-06-21 2005-09-13 Howard I. Maibach Topical administration of pharmacologically active bases in the treatment of inflammatory dermatoses
US7731947B2 (en) * 2003-11-17 2010-06-08 Intarcia Therapeutics, Inc. Composition and dosage form comprising an interferon particle formulation and suspending vehicle
CN100534334C (en) * 2003-09-09 2009-09-02 3M创新有限公司 Concentrated antimicrobial compositions and methods
US20050058673A1 (en) * 2003-09-09 2005-03-17 3M Innovative Properties Company Antimicrobial compositions and methods
DE102004032265A1 (en) * 2004-03-18 2005-09-29 Henkel Kgaa Use of a substance, which inhibits body odor causing gram-positive anaerobic cocci, in a cosmetic deodarant- or antitranspirant-composition to reduce the body odor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0629347A1 (en) * 1992-01-23 1994-12-21 Morinaga Milk Industry Co., Ltd. Antibacterial agent and treatment of article therewith
JPH05229915A (en) * 1992-02-24 1993-09-07 Kanebo Ltd Skin external preparation
CN1172615A (en) * 1996-07-01 1998-02-11 三菱化学食品株式会社 Anti-bacteria agent
CN1313086A (en) * 2000-02-15 2001-09-19 欧莱雅 Use of fatty materials for prevention or reduction of microorganism adhere on skin and/or mucous membrane

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HIROYUKI WAKABAYASHI ET AL: "Increased Stephylococcus-killing Activity of an Antimicrobial Peptide, Lactoferricin B,with Minocycline and Monoacylglycerol", 《BIOSCI. BIOTECHNOL. BIOCHEM.》 *
JON J.KABARA ET AL: "Fatty Acids and Derivatives as Antimicrobial Agents", 《ANTIMICROBIAL AGENTS AND CHEMOTHERAYP》 *
李云堂: "新型食品防腐剂", 《食品科学》 *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10117823B2 (en) 2013-03-12 2018-11-06 Primal Therapies, Inc. Dental composition comprising chelator and base
CN105611909A (en) * 2013-03-12 2016-05-25 艾米丽·A·斯坦 Dental composition comprising chelating agent and base
CN105611909B (en) * 2013-03-12 2020-09-15 普莱玛疗法公司 Dental compositions comprising chelating agents and bases
US11491100B2 (en) 2013-03-12 2022-11-08 Primal Therapies, Inc. Dermal composition comprising chelator and base
CN107709349A (en) * 2015-05-20 2018-02-16 阿比尔技术公司 Composition of plant extracts and the method for preparing it
US10959442B2 (en) 2015-05-20 2021-03-30 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US11160287B2 (en) 2015-05-20 2021-11-02 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
CN107709349B (en) * 2015-05-20 2022-01-28 阿比尔技术公司 Plant extract composition and method for preparing the same
US11812758B2 (en) 2015-05-20 2023-11-14 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US11767278B2 (en) 2015-12-10 2023-09-26 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US11028030B2 (en) 2015-12-10 2021-06-08 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
CN109512998A (en) * 2016-03-04 2019-03-26 广州英赛特生物技术有限公司 The application of synergetic effect additive of the esterification derivative of oxygen-containing hydrocarbon derivative as polymyxins
US11319275B2 (en) 2016-11-17 2022-05-03 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US11918003B2 (en) 2016-11-17 2024-03-05 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof

Also Published As

Publication number Publication date
BRPI0414193A (en) 2006-10-31
WO2005022998A2 (en) 2005-03-17
EP1662873B1 (en) 2016-01-13
MXPA06002719A (en) 2006-09-04
CN1867251A (en) 2006-11-22
JP2007505125A (en) 2007-03-08
ZA200602885B (en) 2007-09-26
KR20060095756A (en) 2006-09-01
US20160095313A1 (en) 2016-04-07
EP1662873A2 (en) 2006-06-07
US20050053593A1 (en) 2005-03-10
WO2005022998A3 (en) 2005-08-04
AU2011201338A1 (en) 2011-04-14
AU2004270258A1 (en) 2005-03-17
CA2538103A1 (en) 2005-03-17

Similar Documents

Publication Publication Date Title
CN102845422A (en) Antimicrobial compositions and methods
AU2004270266B2 (en) Concentrated antimicrobial compositions and methods
CA1331559C (en) Antimicrobial preservative compositions and methods
HUE028283T2 (en) Water and food preservatives
CN104349673A (en) Synergistic antimicrobial agents
JP2010059149A (en) Antibacterial agent and disinfecting method
EP1993355B1 (en) Biofilm formation inhibitor composition
CN101801223A (en) Use of fatty acid esters of glycerol combined with polylysine against gram-negative bacteria
AU5036699A (en) Antimicrobial composition
JP2006001911A (en) Composition for foam sterilization / disinfection / cleaning agent
US10932484B2 (en) Inhibitory activity of acetogenins against Listeria monocytogenes
JP2010270014A (en) Nisin stabilizer
Emami et al. The effect of free and encapsulated essential oil and extract of cinnamon with nanoliposome on Listeria monocytogenes and Escherichia coli inoculated into ground beef
Davidson et al. Medium-Chain Fatty Acids (> C8) and Monoesters
AU2013211535A1 (en) Antimicrobial compositions and methods
Thormar et al. Antimicrobial lipids as disinfectants, antiseptics and sanitizers
JP4904479B2 (en) Nisin-containing detergent composition
RU2802066C1 (en) Detergent
WO2020229202A1 (en) Lactylate blend for preservative/antimicrobial system

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20130102